#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:46:57 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178405 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/26/4022643.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4022643
loop_
_publ_author_name
'Jonathan Clayden'
'Loïc Lemiègre'
'Madeleine Helliwell'
_publ_contact_author_address
; 
Department of Chemistry 
University of Manchester 
Manchester M13 9PL 
England  UK 
;
_publ_contact_author_email       jrtest@spec.ch.man.ac.uk
_publ_contact_author_fax         44(161)275-4734
_publ_contact_author_name        'Raftery, James'
_publ_contact_author_phone       44(161)275-4700
_publ_section_title
;
 Synthesis and Stacked Conformations of Symmetrical and Unsymmetrical
 Oligo-ureas of Metaphenylenediamine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2302
_journal_page_last               2308
_journal_paper_doi               10.1021/jo061989w
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C30 H38 N4 O2'
_chemical_formula_weight         486.64
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.709(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.3864(19)
_cell_length_b                   8.7037(13)
_cell_length_c                   23.480(3)
_cell_measurement_reflns_used    input
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.176
_cell_measurement_theta_min      2.7895
_cell_volume                     2722.2(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_sigmaI/netI    0.0504
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            11294
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9851
_exptl_absorpt_correction_T_min  0.9778
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         3243
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.974
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0581P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1056
_reflns_number_gt                2438
_reflns_number_total             3243
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo061989wsi20060927_091008.cif
_cod_data_source_block           s2036m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4022643
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.97547(9) -0.01404(14) 0.60430(5) 0.0189(3) Uani 1 1 d .
C2 C 1.04503(10) -0.13349(14) 0.60639(5) 0.0235(3) Uani 1 1 d .
H2 H 1.0223 -0.2369 0.6054 0.028 Uiso 1 1 calc R
C3 C 1.14661(10) -0.10315(16) 0.60986(5) 0.0268(3) Uani 1 1 d .
H3 H 1.1937 -0.1850 0.6109 0.032 Uiso 1 1 calc R
C4 C 1.17912(10) 0.04773(16) 0.61184(5) 0.0262(3) Uani 1 1 d .
H4 H 1.2489 0.0698 0.6147 0.031 Uiso 1 1 calc R
C5 C 1.11026(9) 0.16685(15) 0.60966(5) 0.0222(3) Uani 1 1 d .
H5 H 1.1338 0.2699 0.6113 0.027 Uiso 1 1 calc R
C6 C 1.00697(9) 0.13886(14) 0.60516(5) 0.0183(3) Uani 1 1 d .
C7 C 0.93554(9) 0.27492(14) 0.59956(5) 0.0209(3) Uani 1 1 d .
H7 H 0.8653 0.2346 0.5976 0.025 Uiso 1 1 calc R
C8 C 0.94674(11) 0.36456(16) 0.54449(6) 0.0327(3) Uani 1 1 d .
H8A H 1.0142 0.4092 0.5463 0.049 Uiso 1 1 calc R
H8B H 0.8966 0.4469 0.5403 0.049 Uiso 1 1 calc R
H8C H 0.9366 0.2950 0.5116 0.049 Uiso 1 1 calc R
C9 C 0.95211(10) 0.38179(15) 0.65117(6) 0.0289(3) Uani 1 1 d .
H9A H 0.9409 0.3250 0.6860 0.043 Uiso 1 1 calc R
H9B H 0.9050 0.4680 0.6463 0.043 Uiso 1 1 calc R
H9C H 1.0211 0.4210 0.6543 0.043 Uiso 1 1 calc R
C10 C 0.82919(11) -0.08779(17) 0.53898(6) 0.0328(3) Uani 1 1 d .
H10A H 0.7648 -0.1410 0.5394 0.049 Uiso 1 1 calc R
H10B H 0.8761 -0.1533 0.5206 0.049 Uiso 1 1 calc R
H10C H 0.8191 0.0086 0.5176 0.049 Uiso 1 1 calc R
C11 C 0.80347(9) -0.00428(13) 0.63436(5) 0.0196(3) Uani 1 1 d .
C12 C 0.77136(10) 0.09179(16) 0.72729(6) 0.0274(3) Uani 1 1 d .
H12A H 0.7308 0.1708 0.7062 0.041 Uiso 1 1 calc R
H12B H 0.8091 0.1381 0.7609 0.041 Uiso 1 1 calc R
H12C H 0.7272 0.0111 0.7397 0.041 Uiso 1 1 calc R
C13 C 0.92285(8) -0.06045(14) 0.71902(5) 0.0182(3) Uani 1 1 d .
C14 C 0.92254(9) -0.22011(14) 0.71930(5) 0.0209(3) Uani 1 1 d .
H14 H 0.8694 -0.2748 0.6985 0.025 Uiso 1 1 calc R
C15 C 1.0000 -0.2993(2) 0.7500 0.0224(4) Uani 1 2 d S
H15 H 1.0000 -0.4084 0.7500 0.027 Uiso 1 2 calc SR
C16 C 1.0000 0.01846(19) 0.7500 0.0185(4) Uani 1 2 d S
H16 H 1.0000 0.1276 0.7500 0.022 Uiso 1 2 calc SR
N1 N 0.87043(8) -0.05441(11) 0.59776(4) 0.0207(2) Uani 1 1 d .
N2 N 0.84149(7) 0.02498(11) 0.69018(4) 0.0201(2) Uani 1 1 d .
O1 O 0.71407(6) 0.01568(10) 0.61845(4) 0.0253(2) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
C2 C1 C6 120.74(11) .
C2 C1 N1 117.58(11) .
C6 C1 N1 121.58(10) .
C3 C2 C1 120.70(12) .
C3 C2 H2 119.6 .
C1 C2 H2 119.6 .
C2 C3 C4 119.26(12) .
C2 C3 H3 120.4 .
C4 C3 H3 120.4 .
C3 C4 C5 120.24(12) .
C3 C4 H4 119.9 .
C5 C4 H4 119.9 .
C4 C5 C6 121.48(12) .
C4 C5 H5 119.3 .
C6 C5 H5 119.3 .
C1 C6 C5 117.55(11) .
C1 C6 C7 123.74(11) .
C5 C6 C7 118.69(11) .
C6 C7 C9 111.46(10) .
C6 C7 C8 110.90(10) .
C9 C7 C8 109.96(11) .
C6 C7 H7 108.1 .
C9 C7 H7 108.1 .
C8 C7 H7 108.1 .
C7 C8 H8A 109.5 .
C7 C8 H8B 109.5 .
H8A C8 H8B 109.5 .
C7 C8 H8C 109.5 .
H8A C8 H8C 109.5 .
H8B C8 H8C 109.5 .
C7 C9 H9A 109.5 .
C7 C9 H9B 109.5 .
H9A C9 H9B 109.5 .
C7 C9 H9C 109.5 .
H9A C9 H9C 109.5 .
H9B C9 H9C 109.5 .
N1 C10 H10A 109.5 .
N1 C10 H10B 109.5 .
H10A C10 H10B 109.5 .
N1 C10 H10C 109.5 .
H10A C10 H10C 109.5 .
H10B C10 H10C 109.5 .
O1 C11 N1 122.05(11) .
O1 C11 N2 121.17(11) .
N1 C11 N2 116.78(10) .
N2 C12 H12A 109.5 .
N2 C12 H12B 109.5 .
H12A C12 H12B 109.5 .
N2 C12 H12C 109.5 .
H12A C12 H12C 109.5 .
H12B C12 H12C 109.5 .
C16 C13 C14 119.73(12) .
C16 C13 N2 118.90(11) .
C14 C13 N2 121.26(11) .
C15 C14 C13 119.80(12) .
C15 C14 H14 120.1 .
C13 C14 H14 120.1 .
C14 C15 C14 120.39(16) 2_756
C14 C15 H15 119.8 2_756
C14 C15 H15 119.8 .
C13 C16 C13 120.54(16) 2_756
C13 C16 H16 119.7 2_756
C13 C16 H16 119.7 .
C11 N1 C1 123.09(10) .
C11 N1 C10 116.41(10) .
C1 N1 C10 114.89(10) .
C11 N2 C13 122.95(10) .
C11 N2 C12 116.14(10) .
C13 N2 C12 115.31(10) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.3932(17) .
C1 C6 1.3956(17) .
C1 N1 1.4426(15) .
C2 C3 1.3796(18) .
C2 H2 0.9500 .
C3 C4 1.3828(19) .
C3 H3 0.9500 .
C4 C5 1.3849(18) .
C4 H4 0.9500 .
C5 C6 1.3977(17) .
C5 H5 0.9500 .
C6 C7 1.5194(17) .
C7 C9 1.5262(18) .
C7 C8 1.5305(18) .
C7 H7 1.0000 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 N1 1.4636(16) .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 O1 1.2302(14) .
C11 N1 1.3733(15) .
C11 N2 1.3816(16) .
C12 N2 1.4634(15) .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 C16 1.3848(14) .
C13 C14 1.3897(17) .
C13 N2 1.4321(15) .
C14 C15 1.3859(15) .
C14 H14 0.9500 .
C15 C14 1.3859(15) 2_756
C15 H15 0.9500 .
C16 C13 1.3848(14) 2_756
C16 H16 0.9500 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 0.58(19) .
N1 C1 C2 C3 176.92(11) .
C1 C2 C3 C4 0.63(19) .
C2 C3 C4 C5 -0.76(19) .
C3 C4 C5 C6 -0.32(19) .
C2 C1 C6 C5 -1.60(17) .
N1 C1 C6 C5 -177.80(10) .
C2 C1 C6 C7 176.33(11) .
N1 C1 C6 C7 0.13(18) .
C4 C5 C6 C1 1.49(18) .
C4 C5 C6 C7 -176.56(11) .
C1 C6 C7 C9 121.94(13) .
C5 C6 C7 C9 -60.15(14) .
C1 C6 C7 C8 -115.19(13) .
C5 C6 C7 C8 62.73(15) .
C16 C13 C14 C15 -0.76(15) .
N2 C13 C14 C15 -176.77(9) .
C13 C14 C15 C14 0.37(8) 2_756
C14 C13 C16 C13 0.38(8) 2_756
N2 C13 C16 C13 176.49(11) 2_756
O1 C11 N1 C1 150.29(12) .
N2 C11 N1 C1 -28.88(16) .
O1 C11 N1 C10 -1.91(17) .
N2 C11 N1 C10 178.92(11) .
C2 C1 N1 C11 126.13(13) .
C6 C1 N1 C11 -57.55(16) .
C2 C1 N1 C10 -81.29(14) .
C6 C1 N1 C10 95.02(14) .
O1 C11 N2 C13 147.66(11) .
N1 C11 N2 C13 -33.16(16) .
O1 C11 N2 C12 -4.66(17) .
N1 C11 N2 C12 174.52(10) .
C16 C13 N2 C11 134.16(11) .
C14 C13 N2 C11 -49.79(16) .
C16 C13 N2 C12 -73.31(13) .
C14 C13 N2 C12 102.74(13) .
